CH142342A - Process for the preparation of an amide of a heterocyclic carboxylic acid. - Google Patents
Process for the preparation of an amide of a heterocyclic carboxylic acid.Info
- Publication number
- CH142342A CH142342A CH142342DA CH142342A CH 142342 A CH142342 A CH 142342A CH 142342D A CH142342D A CH 142342DA CH 142342 A CH142342 A CH 142342A
- Authority
- CH
- Switzerland
- Prior art keywords
- amide
- preparation
- hydrogenation
- carboxylic acid
- carried out
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Darstellung eines Amides einer heteroeyeliselien Carbousäure. Es wurde gefunden, dass inan zu einem Amid einer heterocyclischen Carbonsäure ge langen kann, indem inan das l#Ticotyl-p-plie- nyläthylainid hydriert. Als Hydrierungsmittel sind zum Beispiel Wasserstoff in Gegenwart katalytisch wirkender Metalle oder Metall gemische, Alkalimetalle in Gegenwart eines Alkohols oder Metalle und Säuren zu nennen.
Das Nipecotyl-,3-pliellylätliylaniid besteht aus glasklaren Prismen von unscharfem, ge- geil 100 liegendem Schmelzpunkt. Es ist in den meisten organischen Lösungsmitteln lös lich. 11'6t Säuren werden leicht lösliche, neu trale Salze erhalten.
Die neue Verbindung kann entweder selbst therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung pharmazeutischer Verbindungen dienen.
Beispiel: 78 Teile Nicotyl-d-pheliyläthylamid (er halten durch Zusammenschmelzen voll Nieo- tinsäurechlorid und @-Plienyläthylamin-chlor- hydrat; Schmelzpunkt<B>82-830)</B> werden mit 300 Teilen Dekalin und 15 Teilen Nickel katalysator unter 40-70 Atmosphären Was serstoffdruck auf 160-168 erhitzt. Nach Beendigung der Wasserstoffaufnahme wird der Autoklaveninhalt mit Alkohol verdünnt, der Katalysator abfiltriert und das Filtrat konzentriert.
Auf Zusatz von etwas Äther kristallisiert das Nipecotyl-@-phenyläthylamid aus.
Die Hydrierung gelingt in gleicher Weise zum Beispiel bei Anwendung von Natrium und Alkohol oder voll Zink in Gegenwart einer Säure.
Process for the preparation of an amide of a heteroeyeliselien carbous acid. It has been found that inan an amide of a heterocyclic carboxylic acid can be obtained by hydrogenating the l # ticotyl-p-plienylethylaamide inanan. Examples of hydrogenating agents that may be mentioned are hydrogen in the presence of catalytically active metals or metal mixtures, alkali metals in the presence of an alcohol or metals and acids.
The nipecotyl-, 3-pliellylätliylaniid consists of crystal-clear prisms with a fuzzy, cool melting point. It is soluble in most organic solvents. Easily soluble, neutral salts are obtained.
The new compound can either find therapeutic use in its own right or serve as an intermediate for the preparation of pharmaceutical compounds.
Example: 78 parts of nicotyl-d-pheliylethylamide (obtained by melting together full of nieotinic acid chloride and @ -plienylethylamine chlorohydrate; melting point 82-830) are mixed with 300 parts of decalin and 15 parts of nickel as a catalyst 40-70 atmospheres hydrogen pressure heated to 160-168. After the uptake of hydrogen has ceased, the contents of the autoclave are diluted with alcohol, the catalyst is filtered off and the filtrate is concentrated.
Upon addition of a little ether, the nipecotyl - @ - phenylethylamide crystallizes out.
The hydrogenation succeeds in the same way, for example when using sodium and alcohol or full zinc in the presence of an acid.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH139805T | 1928-07-24 | ||
CH142342T | 1928-07-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH142342A true CH142342A (en) | 1930-09-15 |
Family
ID=25713398
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH142342D CH142342A (en) | 1928-07-24 | 1928-07-24 | Process for the preparation of an amide of a heterocyclic carboxylic acid. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH142342A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4744459A (en) * | 1980-12-18 | 1988-05-17 | Ryan Patrick J | Method and apparatus for accumulating stockpiles of flowable solid material |
-
1928
- 1928-07-24 CH CH142342D patent/CH142342A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4744459A (en) * | 1980-12-18 | 1988-05-17 | Ryan Patrick J | Method and apparatus for accumulating stockpiles of flowable solid material |
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